


Looks May Deceive

by thelonelywriter



Category: Supernatural
Genre: Alternate Universe - Office, Anal Fingering, Anal Sex, Bottom Dean, Dirty Talk, Episode: s04e17 It's a Terrible Life, M/M, Oral Sex, Plot What Plot, Porn Without Plot, Riding, Rough Sex, Shameless Smut, Smut, Top Castiel
Language: English
Status: Completed
Published: 2015-08-23
Updated: 2015-08-23
Packaged: 2018-04-16 18:58:32
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,010
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4636545
Author URL: https://archiveofourown.org/users/thelonelywriter/pseuds/thelonelywriter
Summary: <blockquote class="userstuff">
              <p>Dean Smith was one hundred percent sure that Castiel Novak, his assistant, was the most vanilla man to exist. He wasn’t exactly boring, it wasn’t that he was bland, he was just… innocent. He was very innocent. So Dean <i>thought</i>. </p><p>Castiel had been Dean’s assistant for over a few months, and the two had a regular, business relationship. Of course, they shared the occasional joke or moment of regular conversation, but it never got to the level that Dean wanted it to get at. Which was Cas’ dick pounding into him.</p>
            </blockquote>





	Looks May Deceive

**Author's Note:**

  * For [Valentia](https://archiveofourown.org/users/Valentia/gifts).



> So, sorry this fic took so long, the thirty day challenge was pretty time consuming, but here it is, as promised!!! I hope you like it, sorry if there are any mistakes, it's currently like three a.m. so I'm just trying to stay awake!!

Dean Smith was one hundred percent sure that Castiel Novak, his assistant, was the most vanilla man to exist. He wasn’t exactly boring, it wasn’t that he was bland, he was just… innocent. He was very innocent. So Dean _thought_. 

Castiel had been Dean’s assistant for over a few months, and the two had a regular, business relationship. Of course, they shared the occasional joke or moment of regular conversation, but it never got to the level that Dean wanted it to get at. Which was Cas’ dick pounding into him.

Dean knew that it was wrong to fantasize about the man he saw nearly every day, but he couldn’t help but think of him in ways that were _definitely_ not vanilla. Dean wanted to ask Castiel out, but he knew that it wasn’t good to have a behind the scenes relationship with a coworker, and he did not want to lose Castiel as either an assistant or a metaphorical boyfriend.

But after a long session of thinking, a couple of self induced orgasms, and a few drinks later, Dean Winchester was coming to the conclusion that he would ask Castiel out. So he did.

It was a Friday afternoon, and most people had already left, but Castiel lingered in Dean’s office as he jotted down a few notes. “Is there anything else, Mr. Smith?” Castiel asked in that particular voice that always got Dean in some way, whether it be flustered, or adoring, or anything else. He could feel his hand sweating as he shot Cas a nervous smile, then looked down.

“Heya, Cas? You wouldn’t happen to be free tomorrow, would you?” Dean asked slowly. Dean watched it dawn on Castiel’s face, even though it took a minute.

“Are you… asking me out?” he questioned cautiously. Dean nodded shyly, and Castiel wore a grin that could have lit up the world. “I would love to,” he responded quickly. Dean looked up eagerly, smiling back at Castiel.

“Great, good, that’s, yeah, okay,” Dean breathed out, his heart racing. “We can meet at that Italian restaurant a few streets over at seven, you know, if you’d like,” Dean proposed, and Castiel nodded furiously.

“Yes, of course, that sounds very nice,” he spluttered, gathering his things. “So I’ll, uh, see you then,” Castiel said with a soft smile, tripping over his own feet before he left, Dean grinning the whole time. Dean hadn't been that happy in a long time.

\---

Dean always thought a kiss on the cheek was ideal for a first date. So, that's how it went. Dean led Cas through his dating regimen, going slowly at first because, after all, Castiel seemed so new to it, and Dean, in the pit of his stomach, feared that he would actually _corrupt Castiel Novak_. What a fallacy.

It was on the tenth date when Dean suggested they go back to his apartment, and it was on the tenth date that once Dean shut the door, Castiel pounced, pinning Dean to the wall. Dean, utterly taken aback, looked into Castiel's eyes. They were hungry, no longer doe eyed and sparkling blue, but a deep blue sparkling with lust. Castiel chuckled, his body inches away from Dean. "Bet you thought I was gonna be a cute, little submissive who would fuck you nice and slow, and orgasm after the first thirty seconds," Castiel cooed, and Dean's dick was already taking great interest in the display. "Sorry, babe, but I think you misread me," he whispered against the shell of Dean's ear. 

Castiel brushed his lips over Dean's jaw before connecting his lips with Dean's, kissing him slowly at first as they had done in the past. But then, Dean thought, _'well, screw that,'_ and parted his lips, inviting Castiel's tongue in. 

They had done that before, they had gotten to the makeout stage in their relationship, but they had never gotten far enough for Castiel's tongue to move with a grace it hadn't quite possessed before, with a alluring ease and roughness that bleed into their bodies so that each man was beginning to lust for more. 

Castiel pulled away, taking Dean's lower lip in his teeth, biting it before letting it go. "Naughty, isn't it, Sir? The big bad boss getting fucked by his meek assistant?" he murmured, pressing his body right up against Dean's. "How dirty," he commented in a low voice, his hands smoothly sliding Dean's jacket off. Dean just let out a little squeak in response because he never thought he would actually hear the gruff voice of Castiel speaking those words in his ear with his body pressed up against Dean's. 

Castiel simply chuckled, pressing and biting bruising kisses into Dean's skin. "Now, of course, if you'd like to wait until the twentieth date for the rough fucking and the dirty talk, we can do that too," Castiel began, toying with the hem of Dean's shirt. "But I get the feeling that you _really_ like having a cock up your ass and a low voice to tell you dirty things," Castiel whispered. "I could always be wrong though," he stated, glancing up at Dean, who looked at him in awe. 

"N- no, you aren't, um, wrong," Dean spluttered out to Castiel’s great pleasure. He grinned, his hands sliding down to Dean’s waist.

“Well then, are we on the same page?” Castiel inquired, staring Dean down. Dean did not have to hesitate because this was like a dream come true for him.

“Fuck, yes,” he breathed out before cupping the sides of Castiel’s face, smashing their lips together. Castiel grinned into the kiss, his hands tightening on Dean's waist as his tongue slid through Dean's mouth with a fiery sort of passion that had Dean letting out soft little noises of pleasure. 

Dean became completely pliant in Castiel's hands as he tugged at the hem of Dean's t-shirt, and Dean pulled it off, breaking the kiss only once. “You know you don’t really seem like this, um, well, you don’t exactly give off-”

“Yeah, I know, I seem sweet, and sensitive, and virginal,” Castiel cut him off. He huffed a breath of laughter, his hands wandering down to the edge of Dean’s jeans. “I think you’re starting to get the gist that I’m not exactly the same when it comes to sex,” he told Dean with a sly smile. 

“Yeah, I’m definitely getting that vibe,” Dean groaned as Castiel rocked his hips down agonizingly slow, letting Dean feel his hardening cock beneath his jeans. Dean let out a soft noise as Castiel moved his lips over his skin, ghosting them over his collarbone, biting hard, and sucking harsh, reddening bruises that had Dean digging his fingertips into Castiel’s back.

Dean’s hands eventually found the edge of Castiel’s jeans, and slipped in a his thumbs as a silent question. Castiel pulled away, kissing the last bruise before he spoke simply. “Where’s your bedroom?” he panted, and Dean immediately kissed him again sloppily as he pulled him towards the bedroom, and Castiel turned their position, throwing Dean down on the bed. He smiled, stepping closer and toying with the button on Dean’s jeans. “May I?” he asked, and Dean was answering nearly before Cas was done talking.

“Please, yes,” he breathed out, watching Castiel straddle him, moving down his body so his face was right where Dean wanted it. 

Deft fingers undid the button and zipper, then pulled Dean’s jeans and boxers down, and Castiel helped Dean kick them to the side. Immediately he brought a hand down and wrapped it around Dean’s cock. Dean sighed softly at the long awaited feeling of Cas’ hand, and Castiel bit his lip at the long awaited sight of Dean’s dick. “Mmm, you know how many times I thought about this?” Castiel asked, giving Dean’s dick a firm stroke as Dean let out a shaky breath.

“No,” Dean answered, then felt the weight of the bed shift, and looked up to see Castiel shimmying out of his jeans and boxers, achingly hard cock springing free before he crawled back on the bed with a sly little grin.

“I thought about it a lot,” he began, slowly draping himself over Dean, his erection jutting against Dean’s hip. “I thought about your body,” he started, his hands running over Dean’s sides. “Thought about this pretty dick of yours,” he cooed, slipping a hand between them and making a fist around Dean’s dick once again. “But most of all, I thought about fucking you, how I’d fuck you, where I’d fuck you,” he whispered into Dean’s ear. “What did you think of, Dean?” Castiel inquired, nipping Dean’s ear. “Don’t be afraid to tell me, even if it’s dirty,” he purred, and goosebumps erupted on Dean’s skin as he blushed.

“I thought about you on your knees for me, of you fucking me hard,” he began, sighing as Castiel let out another purr, nuzzling into his neck to nip and bite there.

“Did you like thinking about me at the office? When I was right there in front of you?” Dean nodded, and Castiel smiled into Dean’s skin. “I bet you liked looking in those virginal eyes thinking of corrupting me, having me fuck you so hard you couldn’t walk the next day,” he started in a low voice, beginning to rut into Dean. “Did you think about me when you touched yourself at night, Mr. Winchester?” Castiel asked, and there was a hint of amusement to his voice.

“God, yes,” Dean choked out with a groan, his hands that were cupping Castiel’s shoulder blades moving down, caressing over his back then stopping, grabbing his ass, and pulling him forward. Castiel chuckled, moving forward to kiss Dean sloppily.

“Mmm, yeah I know you’ve been waiting to grab my ass for the longest time, haven’t you?” Castiel murmured against Dean’s lips.

“Fuck, yes,” Dean growled back, and Castiel grinned widely, and began shimmying back down Dean’s body. Dean looked at him with a tint of confusion, but Castiel just kept grinning. Then, Dean understood once Castiel was sitting between his legs, eyeing Dean’s cock and licking his lips.

“You were right to think of me on my knees. I give great blowjobs,” he told Dean with a sly smirk before he leaned down, and took the head of Dean’s cock in his mouth.

Dean’s hands gripped the sheets as he felt Castiel’s tongue work deftly around the tip, doing things Dean had never done nor had done to him that had him already holding back loud moans. Castiel took his other hand, wrapping it around what wasn’t already in his mouth, and stroking steadily over it, looking up and catching eye contact with Dean, who looked like a complete mess. His hair was mussed, his eyes lust filled, cheeks and chest flushed pink, and it was the exact way that Castiel had dreamed he would look like in a situation like this.

Castiel held eye contact as he sank lower down onto Dean’s dick, smoothing one hand over Dean’s thighs as he did do. “Jesus Christ, Cas,” Dean groaned, his head falling back in pleasure as Castiel moved up and down his shaft, his hand still moving over what wasn’t in his mouth. Dean was so lost in the amazing feeling of Castiel’s mouth that was only going lower and lower, that he only just felt his orgasm approaching quickly before it halted altogether. Castiel pulled off with a wet pop, sitting back on the bed. Dean looked up at him with a, _‘what the fuck?’_ look, and Castiel chuckled a bit.

“I know you’d love to come down my throat, and trust me, I would love to swallow you, but,” he started, crawling forwards until he was straddling Dean. “I’d much rather watch you ride me and come on my cock alone,” he whispered. He grinned, then scooted closer, murmuring into Dean’s ear. “I’ll give you even better oral afterwards if you’re real good for me.” Dean immediately nodded, speechless, and Castiel smiled before giving him a kiss. "Where's the lube?" Castiel asked as his hands wandered over Dean's body.

"Bedside table drawer. Condoms are there too," Dean said softly as he looked up at Castiel with awe. This was not the Castiel he had bargained for, but he was real fucking glad he did.

Castiel crawled over to bedside table, opening it to find just what he was looking for. He set aside a condom on top of the table for later, then crawled back between Dean's legs that were now spread wide. Castiel grinned, and ran a hand along his thigh. "How obedient," he said softly, looking down at Dean. "I didn't even have to tell you to spread those gorgeous legs of yours," Castiel remarked as he opened the lube, and poured a generous amount onto one finger. He brought it slowly down to Dean's rim, and Dean relaxed into the touch, letting Castiel push it in slowly.

Castiel was surprisingly gentle as he worked Dean open, something Dean didn't quite expect. But he had to remember that this was Castiel, and Castiel was a gentle person, even if he was incredibly dominant during sex.

When he slipped in a second finger, and Dean took in the sensations, he realized just how nimble Castiel's fingers were. They were perfect really, and they were even better when Castiel crooked them skillfully to find exactly what he was looking for. "Oh God, right there," Dean managed to groan, and Castiel grinned wickedly, teasing over Dean's prostate, making a routine of passing over it as his fingers worked quickly inside of Dean. 

He wasted no time adding a third finger, thrusting them in and out until Dean was nearly begging for more, and Castiel just had to abide, taking his fingers out, and going to grab the condom packet. Castiel tore it open and slipped it on with ease. He surged forward one last time to kiss Dean messily before he flipped them over, and grinned into the kiss. Dean pulled away slightly, and Castiel was met with the sight of green eyes simply sparkling with hunger, with lust. "Well, go ahead, baby," Castiel said quietly, nipping at Dean's bottom lip. "I think we've both been waiting a long time for this," he murmured. 

Dean grinned, moving down Castiel's body and rising up onto his knees. He took Castiel's dick in his hand, then positioned himself, and in one smooth, fluid motion, sank down onto Castiel's dick. Castiel immediately groaned with a pleased little smirk on his face. "Fuck, you feel so much better than I imagined," he told Dean, who huffed a breath of laughter.

"Yeah, I could say the same for you," he replied. Castiel simply wore a smug look as he watched Dean roll his hip down once, then twice. 

"Oh c'mon, Dean, is that the best you've got?" Castiel teased. Dean let out a breath of air, then thrust down harder, his muscles working to let him rise almost all the way up on Castiel's dick, then slam back down. "Yeah, that's better," Castiel commented, reaching out to grasp Dean's thighs. "But I bet you fantasized about it harder, bet you saw yourself fucking down on my cock so hard neither of us could barely breath," Castiel began, and with every word, Dean was pounding down harder and harder. "Give me all you've got baby, let me see just how beautiful you look up there on my cock," Castiel growled right as Castiel hit Dean's prostate. Dean cried out, his head falling back in pleasure as Castiel ground his hips upwards into Dean's.

"Fuck, right there, Cas!" Dean moaned. Castiel arched his back off the bed to give Dean better access, and Dean only went harder, Castiel moaning praises beneath him, whispering filth as Dean felt his body beg for more as he slammed himself down harder and harder until Castiel was digging his nails into Dean's thighs.

"Yeah, just like that, baby," Castiel soothed. "Damn you look so fucking gorgeous up there," he growled, grinding his hips up hard. Dean moaned in response, clutching Cas' sides with bruising fingertips. He could already feel himself getting closer with each downward thrust, with every meeting of their hips that felt like pure pleasure. And meanwhile, there was Castiel, who just wouldn’t stop letting out these noises that were killing Dean, that were music to his ears. His body was slowly flooding with pleasure, and it only to a few words from Cas to push him over the edge.

“C’mon sweetheart, I know you’re close aren’t you? I wanna see you come on my cock, wanna watch you. Know you want to too, don’t you?” he purred, and Dean felt the pleasure inside of him crest as he gripped onto Castiel’s sides painfully hard, moaning Castiel’s name as he came, streaking Castiel’s belly with hot come. Dean’s hips stuttered as the sight sent Castiel into climax too, his back arching off of the bed, his mouth open as he panted Dean’s name over and over until his tensed muscles relaxed, and Dean slipped off of Cas’ dick, collapsing next to Castiel with a huff of air.

The two breathed for a moment before Castiel turned to Dean with a coy smile. “What?” Dean inquired, still partially breathless.

"Best sex ever," he stated simply, and Dean laughed, nodding.

"Yeah, I don't know why this didn't happen sooner," Dean mused. Castiel moved closer to him, giving him a soft kiss.

"It didn't happen sooner because you probably thought I was a virgin," he murmured, and Dean blushed a bit at the truth of the statement.

"Yeah, I guess I was really wrong on that count," Dean huffed, and Castiel simply smiled, snuggling into the crook of Dean's neck.

"You know, that blowjob I offered is still up for grabs," he whispered. Dean could feel his dick twitch at the thought, and he nodded.

"I think I’ll have to take you up on that offer," he whispered back.

**Author's Note:**

> Let me know what you thought, I hope everything in it was okay!! And on a side note, holy wow, first fic after the challenge!! How'd I do guys, do I still got it? :3 Also, as an aside here's [my tumblr :)](http://blueyesintheimpala.tumblr.com)


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